Palladium-mediated cyclization of 6-methyl-1-phenyl-6-hepten-2-one to form 3-methyldiphenylmethane: Carbonyl activation by a neutral palladium(II) complex

Journal Article (Journal Article)

Reaction of 6-methyl-1-phenyl-6-hepten-2-one (4) with a stoichiometric mixture of PdCl (CH CN) (2) and Me SiCl in dioxane at 70 °C formed 3-methyldiphenylmethane (6) in 78% isolated yield. A number of experiments supported a mechanism for the conversion of 4 to 6 initiated by palladium-mediated carbonyl-ene reaction to form the isolable palladium alkene-alcohol complex Pd[η -HOC(Bn) CH C(Me)=CHCH CH ]Cl (7) followed by Me SiCl-mediated dehydration to form the unobserved palladium diene complex Pd[η -C(Bn)=C(Me)CH=CHCH CH ]Cl (II) and palladium-mediated oxidation of II to form 6. © 2007 American Chemical Society. 2 3 2 3 2 2 2 2 3 2 2 2 3 4

Full Text

Duke Authors

Cited Authors

  • Han, X; Widenhoefer, RA

Published Date

  • July 30, 2007

Published In

Volume / Issue

  • 26 / 16

Start / End Page

  • 4061 - 4065

International Standard Serial Number (ISSN)

  • 0276-7333

Digital Object Identifier (DOI)

  • 10.1021/om700379g

Citation Source

  • Scopus